unlikely best friends: styling the outfits that felt a little wrong
the best style happens when you throw out the rulebook.
UNLIKELY BEST FRIENDS: not just for ducklings & dogs
FYI: This post is a little long and might get clipped in your email. For the full experience, open it in the Substack app or on the web.
Last week we enjoyed some family time at the lake. I was staring into the lake abyss doing some deep thinking (so meta) while trying to avoid eye contact with my kids. Their frisbee had sunk to the bottom of the lake, and they were about to ask me for help. Before I knew it, I’d be wading through the entire lake with my feet to help them find it.
I was talking to my husband about some of my closest friends—the ones I’ve had for a long time and the ones I’ve just recently met. I was sharing that some of my closest friends in life end up being people who are so incredibly different from me.
Usually, when I meet you and feel this way, I will quickly do the following:
Tell you I’m an Aquarius.1
Discuss my blood type with you.2
Most Importantly: Declare you my “unlikely best friend.” I will then immediately pull up a photo of two animals that are so damn cute and are known as “unlikely best friends.” I will then assign us two different animals.
Some of you are hysterically laughing reading this because you have been victimized by me in this way.
YOUR UNLIKELY BFF REPORTING FOR STYLE DUTY
I finally paused and thought to myself, am I a lot of people’s unlikely best friend on Substack? Hear me out. There are celebrity stylists and people who work in incredibly impressive roles in the fashion industry who have taught me SO much in the short time I’ve been on Substack.
And then… there’s, well… me. I am a 37 year old mom of two, dog mom to two German Sheps, and a teacher who LOVES to learn, apply, style, and celebrate others.
And there are people who are choosing to subscribe to my publication because either they a. think I’m funny (thank God, because my husband doesn’t laugh at me enough3) or b. it’s a fresh POV from the working mom, wife, trying to be stylish while digging through the creative outlet trenches.
You have people like me, civilian level Substackers, enjoying expressing themselves in creative ways and being cheered on by god damn celebrity stylists. That’s pretty cool.
I think I like being your unlikely best friend!!
PIVOTING TO WEIRD: unlikely best friends in fashion
Alright, now we’re going to pivot even more. The thinking didn’t stop there. I started to think about unlikely best friends in fashion. Hear me out. These are two pieces in a wardrobe that technically shouldn’t work, but somehow do.
For example, remember when I celebrated wearing loafers in the summer last week? That’s quite an unlikely duo: summer = hot, and loafers aren’t exactly the most keep-your-feet-cool, sweat-free kind of shoe. An unlikely best friend!
On paper this style duo is very strange, but when I wore it I LOVED it.
In Katelyn Cnossen’s most recent post, she mentioned something that shows we’re totally on the same wavelength stylistically. She wrote,
“I always gravitate toward unexpected pairings, especially when it comes to footwear. This dress is terry cloth, soft and casual; the Docs are sturdy and bold. A perfect juxtaposition.”
She’s describing a fashion unlikely best friend! Except she says it in a much more sophisticated way, calling it an “unexpected pairing.”
BREAKING THE RULES IS FUN: my styling adventure
A few years ago, I never would’ve taken any fashion-related risks. I was afraid to wear or do anything that made me stand out. It felt shameful if someone acknowledged something on me that was different or unique.
Now, in my ripe late 30’s, I’m feeling more adventurous than ever. I’m excited and willing to try it all. The weirder the better. The more unique, hell yeah.
In a recent post, Kelly Williams, basically reiterated the green light to have fun and try new things. Her advice was:
“Finally, this might be good news or bad news, none of us are JLaw being papped in our outfits, it’s pretty likely that very few people are paying any attention to what you are wearing. The good news on that is that we don’t have to fear embarrassment or judgement.”
It’s true! And that’s exactly what I did. I picked the “trends” or unexpected duos that I like and had a little fun with them. I explored what worked, what didn’t, and what I’d tweak if I did it all over again.
This has led me to sharing with you my personal favorite unlikely best friends in my wardrobe. I’m going to share it with you in the following format:
The unlikely BFF and some inspiration of what this looks like.
My civilian take on the outfit. *I ONLY wore it if it’s something I would actually leave the house in.
Style Notes - my thoughts, reasoning, and potential edits I would make.
Let’s do it!
COMBOS I WOULD REALLY WEAR
Here are a few unexpected fashion combos I’ve been really loving lately!
1. Socks + Loafers
Penny loafers and socks (bonus points if the socks are colorful). It’s the ultimate nod to classic-meets-playful style.
STYLE NOTES:
I love this look. It took a little trial and error to find socks that worked. This pair nailed both the height and the cuteness factor.
I’d even consider swapping out the black tee for a navy tee to make it even more unexpected. WILD.
Every part of me wanted to unbutton the polo’s top button… but I actually liked it better this way.
The polo is such a light luxurious cashmere. Here’s to hoping I don’t destroy it in the wash. (Some of us can’t have nice things)
2. Baseball Hat + Dress
Pairing a casual baseball cap with a more formal outfit adds instant, cool contrast. It’s not groundbreaking or new, but it’s definitely something I’ve never leaned into until now.
STYLING NOTES
This was probably my favorite look to replicate. I loved the mixture of a sporty baseball hat + a layer + cute dress + sneakers. It felt like the right amount of contrast.
My family is always offended when I wear hats for sentimental reasons not team loyalty reasons. I went to college in Boston. My family members are hardcore Yankee fans.
No show for the socks seemed to look best when I wore sneakers due to my ankle anatomy.
I was surprised to see my favorite way to layer with this look was sweater around the waist! This is usually my LEAST go-to choice.
3. Blazer + Casual Attire (you wore a blazer with what!?)
Blazers meets casual attire & athleisure, think tailored jackets paired with sporty pieces.
STYLE NOTES:
I’ve been rocking the cute top and athletic shorts for a while now. But holy cow, I did not plan on liking this outfit this much when I added a blazer.
The big thing running through my mind: the temperature has to be pretty specific for this look. Today it’s 90 degrees, and honestly, everyone’s lucky I’m not just walking around in a bathing suit.
I added a chunky gold earring to elevate the look a bit more.
Tried another combo of dress + blazer, but didn’t love it. Therefore, not pictured.
4. Athletic Shorts + Cute Top (athletic shorts, but no athletics?!)
Adidas shorts plus a cute top is a combo I can’t stop luxuriating in. Add ballet flats, and you’re ready to move and groove.
STYLE NOTES:
Same look, just took off the blazer.
Danielle would agree that red is my gateway color right now.
This combo has been really fun to experiment with this summer and the KEY is that it’s SO. DAMN. COMFORTABLE.
5. Jorts + Designer Energy
Jean shorts paired with heels, polos, and unexpected accessories, sure why not?
STYLE NOTES:
This also addresses the Blazer + Casual Attire combo.
I hate heels more than anything in this life. I always walk like a baby deer when I wear them. But… omg. I love the way these kitten heels look with… jorts?
I didn’t plan to just wear the look with the white tank, but I was really into that one so I had to photo it.
I don’t know why, but I don’t wear my belts in the summer. Definitely helped tie this look together.
I loved it with the blazer, but again, it needs to be a very specific temperature out for me to actually wear this combo. (Hot Girl Summer, the literal kind)
6. Lace Skirts + Structured Top (lace skirts vs. everyone)
Sheer lace skirts can be pretty polarizing. But low-key, I love them. I just hadn’t quite figured out how to style mine… until now. Not every look is exciting and enticing for everyone and that’s totally valid.
STYLE NOTES:
The first image (left) shows my original styling idea from the inspo. Then I got hit with a targeted Instagram video of a stylist creating proportions with a belt. The second picture (right) is definitely how I’d wear it. 10/10 loved it.
I’d probably swap the random leather belt for a rope belt like this.
I’ve seen the skirt paired with sneakers, but I didn’t love that combo on me.
The skirt is sheer. Please note: I am fully protected by nude bike shorts.
7. Babydoll Dress + Sneakers
A dress and sneakers is not unheard of. The babydoll dress is a new-er style for me. This frilly and delicate dress brings the whimsy, while the sneakers keep it grounded.
STYLING NOTES:
I read a Substack Note recently saying it feels like everyone today is wearing pajama-like outfits with Adidas sneakers.
First, I do not wear anything remotely close to this as pajamas. I wear an oversized tee and basketball shorts.
Second, I felt slightly self-conscious for 9 seconds… then I remembered: I STILL LOVE THIS LOOK.
Learning more about my ankle anatomy— shorter socks or no socks is better for me. Didn’t love the ones in my picture to the right.
Nude shorts underneath is a must.
Could’ve gone even wilder by throwing on a baseball hat.
EMBRACING A LITTLE WRONG IN FASHION
Maybe the acceptance of unlikely BFFs in our wardrobes is what makes fashion so fun. The iconic Jenna Lyons (former creative director at J.Crew, fashion icon, and RHONY cast member!!!) once said:
“I like things to feel a touch unfinished; sweatpants with heels, or tennis shoes with a trouser. Those things are important.”
I think she’s spot on.
But really, isn’t that why we’re all here?
To figure out how to add that one unexpected thing!
The piece that makes an outfit feel more personal, more alive.
To feel like our true selves.
To push back against the “rules” a little (or a lot).
To surprise ourselves.
To express ourselves without having to say a word.
Unlikely best friends. Unexpected choices. That’s the REAL magic, my friends!
SIGNING OFF
Welp, that got deeper than I expected. What looks caught your eye? Are there any styles or combos you’re loving right now? Tell me all about them!
I’ll be back next week with a recap of my most recent outfits. For now, stay weird, stay unique, stay unlikely.
Keep it quirky xo,
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The rarest astrological sign. Creative, independent, unconventional, aloof, social but selective, rebellious…. all very on brand for me.
I’m AB+ if you were curious. The “universal recipient.”
We recently went to a comedy show, and I was insanely offended that he was hysterically laughing at the comedian’s jokes, yet doesn’t appreciate mine. Felt very disrespectful.
Love this on multiple levels, from the friends who are perhaps unexpected BFFs, to embracing the wisdom/freedom of aging to add friction. I'm definitely going to do more dress + cap as we head into Australian summer, including to avoid the sun spots! Ps. now also wondering if I'm a pajamas + adidas victim ;)
I loved all the looks above 😍 my favorite one is definitely the red shorts with the jacket, but all had something so stylish about them. The long skirt one makes you look an A type celebrity IMO. I loved this post. Now you have me thinking about unlikely pairings in my wardrobe. My issue is that I generally go for comfort over looks, so when it's warms it's so difficult for me to one to add a jacket to any looks. However, your looks show me that I can experiment more with shoes too if that's what will make me more comfortable 🫶🏻 as always a great read Traci 🤗